人 sits on top - a stylised standing figure. Combined with 止 (foot) underneath, 企 originally pictured a person rising onto their tiptoes to look ahead. The radical here also indexes the character in the person section.
止 is an old foot-print pictograph. Person + foot = standing tall on the toes, straining to see further - the literal sense of 企. From 'looking far' came the modern meanings 'to plan, expect, undertake' and the noun 企业 (enterprise).
